CH633291A5 - Verfahren zur herstellung von pyrimido(1,2-a)benzimidazolderivaten. - Google Patents
Verfahren zur herstellung von pyrimido(1,2-a)benzimidazolderivaten. Download PDFInfo
- Publication number
- CH633291A5 CH633291A5 CH1507777A CH1507777A CH633291A5 CH 633291 A5 CH633291 A5 CH 633291A5 CH 1507777 A CH1507777 A CH 1507777A CH 1507777 A CH1507777 A CH 1507777A CH 633291 A5 CH633291 A5 CH 633291A5
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- CH
- Switzerland
- Prior art keywords
- radical
- carbon atoms
- formula
- hydrogen
- mixture
- Prior art date
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- HOHWYQSDLRTVDK-UHFFFAOYSA-N pyrimido[1,2-a]benzimidazole Chemical class N1=CC=CN2C3=CC=CC=C3N=C21 HOHWYQSDLRTVDK-UHFFFAOYSA-N 0.000 title description 3
- 238000004519 manufacturing process Methods 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims description 34
- 125000004432 carbon atom Chemical group C* 0.000 claims description 20
- -1 cyano, acetyl Chemical group 0.000 claims description 18
- 238000000034 method Methods 0.000 claims description 15
- 229910052739 hydrogen Inorganic materials 0.000 claims description 11
- 239000001257 hydrogen Substances 0.000 claims description 11
- 125000005843 halogen group Chemical group 0.000 claims description 9
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 8
- JWYUFVNJZUSCSM-UHFFFAOYSA-N 2-aminobenzimidazole Chemical compound C1=CC=C2NC(N)=NC2=C1 JWYUFVNJZUSCSM-UHFFFAOYSA-N 0.000 claims description 7
- 239000000460 chlorine Substances 0.000 claims description 7
- 238000006243 chemical reaction Methods 0.000 claims description 6
- 238000002360 preparation method Methods 0.000 claims description 6
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 5
- 229910052801 chlorine Inorganic materials 0.000 claims description 5
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 3
- 239000003701 inert diluent Substances 0.000 claims description 3
- 239000012442 inert solvent Substances 0.000 claims description 3
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 3
- LEVJVKGPFAQPOI-UHFFFAOYSA-N phenylmethanone Chemical compound O=[C]C1=CC=CC=C1 LEVJVKGPFAQPOI-UHFFFAOYSA-N 0.000 claims description 3
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 claims description 2
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 2
- 150000002431 hydrogen Chemical class 0.000 claims 3
- VOLGAXAGEUPBDM-UHFFFAOYSA-N $l^{1}-oxidanylethane Chemical compound CC[O] VOLGAXAGEUPBDM-UHFFFAOYSA-N 0.000 claims 2
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 claims 2
- 239000005977 Ethylene Substances 0.000 claims 1
- 239000002253 acid Substances 0.000 claims 1
- HHFAWKCIHAUFRX-UHFFFAOYSA-N ethoxide Chemical compound CC[O-] HHFAWKCIHAUFRX-UHFFFAOYSA-N 0.000 claims 1
- 239000000203 mixture Substances 0.000 description 43
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 38
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 36
- BAPJBEWLBFYGME-UHFFFAOYSA-N Methyl acrylate Chemical compound COC(=O)C=C BAPJBEWLBFYGME-UHFFFAOYSA-N 0.000 description 32
- 229910052799 carbon Inorganic materials 0.000 description 31
- 150000001721 carbon Chemical group 0.000 description 26
- 238000002844 melting Methods 0.000 description 24
- 230000008018 melting Effects 0.000 description 24
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 18
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- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 16
- DTQVDTLACAAQTR-UHFFFAOYSA-N trifluoroacetic acid Substances OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 16
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 16
- 239000007787 solid Substances 0.000 description 15
- 238000004452 microanalysis Methods 0.000 description 12
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 10
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 10
- 230000004520 agglutination Effects 0.000 description 9
- 238000010992 reflux Methods 0.000 description 9
- 239000007858 starting material Substances 0.000 description 9
- 238000012360 testing method Methods 0.000 description 9
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 8
- ATDGTVJJHBUTRL-UHFFFAOYSA-N cyanogen bromide Chemical compound BrC#N ATDGTVJJHBUTRL-UHFFFAOYSA-N 0.000 description 8
- 238000001914 filtration Methods 0.000 description 8
- SILNNFMWIMZVEQ-UHFFFAOYSA-N 1,3-dihydrobenzimidazol-2-one Chemical compound C1=CC=C2NC(O)=NC2=C1 SILNNFMWIMZVEQ-UHFFFAOYSA-N 0.000 description 6
- XTWYTFMLZFPYCI-KQYNXXCUSA-N 5'-adenylphosphoric acid Chemical compound C1=NC=2C(N)=NC=NC=2N1[C@@H]1O[C@H](COP(O)(=O)OP(O)(O)=O)[C@@H](O)[C@H]1O XTWYTFMLZFPYCI-KQYNXXCUSA-N 0.000 description 6
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- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 5
- 238000003756 stirring Methods 0.000 description 5
- 125000001424 substituent group Chemical group 0.000 description 5
- IFODSVOKJRKVAH-UHFFFAOYSA-N 5,6-di(propan-2-yloxy)-1h-benzimidazol-2-amine Chemical compound C1=C(OC(C)C)C(OC(C)C)=CC2=C1NC(N)=N2 IFODSVOKJRKVAH-UHFFFAOYSA-N 0.000 description 4
- 102000008186 Collagen Human genes 0.000 description 4
- 108010035532 Collagen Proteins 0.000 description 4
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- 241000699670 Mus sp. Species 0.000 description 4
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- 238000001704 evaporation Methods 0.000 description 4
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- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 4
- 239000002244 precipitate Substances 0.000 description 4
- ASVPUUDJBLBNEH-UHFFFAOYSA-N 1-(2-amino-3h-benzimidazol-5-yl)ethanone Chemical compound CC(=O)C1=CC=C2N=C(N)NC2=C1 ASVPUUDJBLBNEH-UHFFFAOYSA-N 0.000 description 3
- XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 3
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- BRSGXKFOEKRYKN-UHFFFAOYSA-N 8-chloro-7-methyl-4,10-dihydro-3h-pyrimido[1,2-a]benzimidazol-2-one Chemical compound N12CCC(=O)NC2=NC2=C1C=C(C)C(Cl)=C2 BRSGXKFOEKRYKN-UHFFFAOYSA-N 0.000 description 3
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- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 3
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical class [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 3
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- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 3
- 229910052794 bromium Inorganic materials 0.000 description 3
- 239000003085 diluting agent Substances 0.000 description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
- 239000000706 filtrate Substances 0.000 description 3
- URLKBWYHVLBVBO-UHFFFAOYSA-N p-dimethylbenzene Natural products CC1=CC=C(C)C=C1 URLKBWYHVLBVBO-UHFFFAOYSA-N 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- 239000000725 suspension Substances 0.000 description 3
- CZDYPVPMEAXLPK-UHFFFAOYSA-N tetramethylsilane Chemical compound C[Si](C)(C)C CZDYPVPMEAXLPK-UHFFFAOYSA-N 0.000 description 3
- 125000004066 1-hydroxyethyl group Chemical group [H]OC([H])([*])C([H])([H])[H] 0.000 description 2
- HYZJCKYKOHLVJF-UHFFFAOYSA-N 1H-benzimidazole Chemical compound C1=CC=C2NC=NC2=C1 HYZJCKYKOHLVJF-UHFFFAOYSA-N 0.000 description 2
- GPMHHSJZGVOEFS-UHFFFAOYSA-N 2-Amino-5-benzoylbenzimidazole Chemical compound C1=C2NC(N)=NC2=CC=C1C(=O)C1=CC=CC=C1 GPMHHSJZGVOEFS-UHFFFAOYSA-N 0.000 description 2
- ZSAWWJYNDFERFN-UHFFFAOYSA-N 4,7-dimethyl-1h-benzimidazol-2-amine Chemical compound CC1=CC=C(C)C2=C1N=C(N)N2 ZSAWWJYNDFERFN-UHFFFAOYSA-N 0.000 description 2
- 125000000242 4-chlorobenzoyl group Chemical group ClC1=CC=C(C(=O)*)C=C1 0.000 description 2
- RRJIGHUKYPLKIW-UHFFFAOYSA-N 5-chloro-6-methyl-1h-benzimidazol-2-amine Chemical compound C1=C(Cl)C(C)=CC2=C1NC(N)=N2 RRJIGHUKYPLKIW-UHFFFAOYSA-N 0.000 description 2
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- WOIHSHXQQGYBGM-UHFFFAOYSA-N 5h-[1,3]dioxolo[4,5-f]benzimidazol-6-amine Chemical compound C1=C2NC(N)=NC2=CC2=C1OCO2 WOIHSHXQQGYBGM-UHFFFAOYSA-N 0.000 description 2
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- IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 2
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 2
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- DPJCXCZTLWNFOH-UHFFFAOYSA-N 2-nitroaniline Chemical compound NC1=CC=CC=C1[N+]([O-])=O DPJCXCZTLWNFOH-UHFFFAOYSA-N 0.000 description 1
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- SPVQXWWWBMKQGE-UHFFFAOYSA-N 4,10-dihydro-3h-pyrimido[1,2-a]benzimidazol-2-one Chemical class C1=CC=C2N3CCC(=O)NC3=NC2=C1 SPVQXWWWBMKQGE-UHFFFAOYSA-N 0.000 description 1
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- HAADRTMPUSJNOI-UHFFFAOYSA-N 5,6-dichloro-1h-benzimidazol-2-amine Chemical compound ClC1=C(Cl)C=C2NC(N)=NC2=C1 HAADRTMPUSJNOI-UHFFFAOYSA-N 0.000 description 1
- POWPTEBMSHLSRA-UHFFFAOYSA-N 5,6-dimethoxy-1h-benzimidazol-2-amine Chemical compound C1=C(OC)C(OC)=CC2=C1NC(N)=N2 POWPTEBMSHLSRA-UHFFFAOYSA-N 0.000 description 1
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- 239000002032 methanolic fraction Substances 0.000 description 1
- 125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 description 1
- YWANGSCDWBUSBK-UHFFFAOYSA-N n-(5-chloro-2-nitrophenyl)acetamide Chemical compound CC(=O)NC1=CC(Cl)=CC=C1[N+]([O-])=O YWANGSCDWBUSBK-UHFFFAOYSA-N 0.000 description 1
- 238000006396 nitration reaction Methods 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- 238000010899 nucleation Methods 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 210000000056 organ Anatomy 0.000 description 1
- 239000000546 pharmaceutical excipient Substances 0.000 description 1
- 239000000825 pharmaceutical preparation Substances 0.000 description 1
- 210000004623 platelet-rich plasma Anatomy 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 238000011321 prophylaxis Methods 0.000 description 1
- 125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000002390 rotary evaporation Methods 0.000 description 1
- 231100000161 signs of toxicity Toxicity 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 239000012265 solid product Substances 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- UIERETOOQGIECD-ONEGZZNKSA-N tiglic acid Chemical compound C\C=C(/C)C(O)=O UIERETOOQGIECD-ONEGZZNKSA-N 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 238000002054 transplantation Methods 0.000 description 1
- 230000002792 vascular Effects 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/04—Ortho-condensed systems
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P7/00—Drugs for disorders of the blood or the extracellular fluid
- A61P7/02—Antithrombotic agents; Anticoagulants; Platelet aggregation inhibitors
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D235/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings
- C07D235/02—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings condensed with carbocyclic rings or ring systems
- C07D235/04—Benzimidazoles; Hydrogenated benzimidazoles
- C07D235/24—Benzimidazoles; Hydrogenated benzimidazoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached in position 2
- C07D235/30—Nitrogen atoms not forming part of a nitro radical
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
- C07D491/02—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains two hetero rings
- C07D491/04—Ortho-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
- C07D491/12—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains three hetero rings
- C07D491/14—Ortho-condensed systems
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Diabetes (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Medicinal Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Hematology (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB51426/76A GB1585965A (en) | 1976-12-09 | 1976-12-09 | 3,4-dihydropyrimido (1,2 - )benzimidazol - 2(1h) - ones |
| GB3334177 | 1977-08-09 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH633291A5 true CH633291A5 (de) | 1982-11-30 |
Family
ID=26261828
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH1507777A CH633291A5 (de) | 1976-12-09 | 1977-12-08 | Verfahren zur herstellung von pyrimido(1,2-a)benzimidazolderivaten. |
Country Status (23)
| Country | Link |
|---|---|
| US (1) | US4167569A (cs) |
| JP (1) | JPS5390296A (cs) |
| AT (1) | AT359068B (cs) |
| AU (1) | AU514427B2 (cs) |
| CA (1) | CA1086727A (cs) |
| CH (1) | CH633291A5 (cs) |
| CS (1) | CS199696B2 (cs) |
| DD (1) | DD133330A5 (cs) |
| DE (1) | DE2754930A1 (cs) |
| ES (1) | ES464862A1 (cs) |
| FI (1) | FI63577C (cs) |
| FR (1) | FR2373543A1 (cs) |
| GR (1) | GR65298B (cs) |
| HU (1) | HU176540B (cs) |
| IE (1) | IE45924B1 (cs) |
| IL (1) | IL53507A (cs) |
| IT (1) | IT1143729B (cs) |
| NL (1) | NL7713658A (cs) |
| NO (1) | NO774216L (cs) |
| NZ (1) | NZ185823A (cs) |
| PL (1) | PL107142B1 (cs) |
| SE (1) | SE435385B (cs) |
| SU (1) | SU843751A3 (cs) |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| IE51802B1 (en) * | 1979-12-03 | 1987-04-01 | Fujisawa Pharmaceutical Co | Quinazoline derivatives,processes for their preparation and pharmaceutical compositions containing them |
| CA1157858A (en) | 1979-12-03 | 1983-11-29 | Ikuo Ueda | Quinazoline derivatives |
| DE3208218A1 (de) * | 1982-03-06 | 1983-09-08 | Basf Ag, 6700 Ludwigshafen | Isoindolinfarbstoffe und deren verwendung |
| RU2394824C1 (ru) * | 2008-12-25 | 2010-07-20 | Государственное научное учреждение Северо-Кавказский зональный научно-исследовательский ветеринарный институт Российской академии сельскохозяйственных наук | ПРОИЗВОДНЫЕ ПИРИДО [1,2-a]БЕНЗИМИДАЗОЛА, ОБЛАДАЮЩИЕ АНТИБАКТЕРИАЛЬНЫМ ДЕЙСТВИЕМ, И СПОСОБ ИХ ПОЛУЧЕНИЯ |
| MY167785A (en) | 2012-06-27 | 2018-09-25 | 4Sg Ag | Bifluorodioxalane-amino-benzimidazole kinase inhibitors for the treatment of cancer, autoimmuneinflammation and cns disorders |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3468888A (en) * | 1967-04-11 | 1969-09-23 | Smithkline Corp | 2-substituted pyrimido(1,2-a) benzimidazoles |
| US3988340A (en) * | 1975-01-23 | 1976-10-26 | Bristol-Myers Company | 6-Alkoxymethyl-1,2,3,5-tetrahydroimidazo[2,1-b]quinazolin-2-ones and 7-alkoxymethyl-6-[H]-1,2,3,4-tetrahydropyrimido[2,1-b]quinazolin-2-ones |
| US4072679A (en) * | 1976-06-15 | 1978-02-07 | E. R. Squibb & Sons, Inc. | 1,4- AND 4,10-DIHYDRO-4-OXO-PYRIMIDO (1,2-A)-benzimidazole-3-carboxylic acids, esters and amides |
-
1977
- 1977-11-23 US US05/855,003 patent/US4167569A/en not_active Expired - Lifetime
- 1977-11-28 IE IE2408/77A patent/IE45924B1/en unknown
- 1977-11-29 CA CA291,976A patent/CA1086727A/en not_active Expired
- 1977-11-30 NZ NZ185823A patent/NZ185823A/xx unknown
- 1977-12-01 IL IL53507A patent/IL53507A/xx unknown
- 1977-12-01 AU AU31121/77A patent/AU514427B2/en not_active Expired
- 1977-12-05 HU HU77IE816A patent/HU176540B/hu unknown
- 1977-12-07 DD DD7700202450A patent/DD133330A5/xx unknown
- 1977-12-07 GR GR54931A patent/GR65298B/el unknown
- 1977-12-07 ES ES464862A patent/ES464862A1/es not_active Expired
- 1977-12-08 NO NO774216A patent/NO774216L/no unknown
- 1977-12-08 SE SE7713958A patent/SE435385B/sv unknown
- 1977-12-08 CH CH1507777A patent/CH633291A5/de not_active IP Right Cessation
- 1977-12-08 PL PL1977202753A patent/PL107142B1/pl unknown
- 1977-12-08 FR FR7737011A patent/FR2373543A1/fr active Granted
- 1977-12-09 NL NL7713658A patent/NL7713658A/xx not_active Application Discontinuation
- 1977-12-09 SU SU772552626A patent/SU843751A3/ru active
- 1977-12-09 AT AT883677A patent/AT359068B/de not_active IP Right Cessation
- 1977-12-09 DE DE19772754930 patent/DE2754930A1/de not_active Withdrawn
- 1977-12-09 IT IT30558/77A patent/IT1143729B/it active
- 1977-12-09 CS CS778270A patent/CS199696B2/cs unknown
- 1977-12-09 JP JP14866977A patent/JPS5390296A/ja active Pending
- 1977-12-09 FI FI773724A patent/FI63577C/fi not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| CA1086727A (en) | 1980-09-30 |
| FR2373543B1 (cs) | 1980-05-16 |
| JPS5390296A (en) | 1978-08-08 |
| SU843751A3 (ru) | 1981-06-30 |
| DD133330A5 (de) | 1978-12-27 |
| GR65298B (en) | 1980-08-01 |
| ATA883677A (de) | 1980-03-15 |
| CS199696B2 (en) | 1980-07-31 |
| IL53507A0 (en) | 1978-03-10 |
| PL202753A1 (pl) | 1978-10-09 |
| US4167569A (en) | 1979-09-11 |
| NL7713658A (nl) | 1978-06-13 |
| AU514427B2 (en) | 1981-02-12 |
| AT359068B (de) | 1980-10-27 |
| AU3112177A (en) | 1979-06-07 |
| NZ185823A (en) | 1980-08-26 |
| DE2754930A1 (de) | 1978-06-15 |
| PL107142B1 (pl) | 1980-01-31 |
| IE45924L (en) | 1978-06-09 |
| SE435385B (sv) | 1984-09-24 |
| HU176540B (en) | 1981-03-28 |
| IT1143729B (it) | 1986-10-22 |
| FR2373543A1 (fr) | 1978-07-07 |
| FI63577C (fi) | 1983-07-11 |
| FI63577B (fi) | 1983-03-31 |
| IE45924B1 (en) | 1982-12-29 |
| SE7713958L (sv) | 1978-06-10 |
| IL53507A (en) | 1981-07-31 |
| ES464862A1 (es) | 1979-01-01 |
| NO774216L (no) | 1978-06-12 |
| FI773724A7 (fi) | 1978-06-10 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PL | Patent ceased | ||
| PL | Patent ceased |